Hydrochloric Acid → HCID 70529065, compound

HRID 1074488Notes

Reaction equation

HRID 1074488 reaction equation
C1O[C:4]2([CH2:9][CH2:8][C@@H:7]([CH2:10][CH:11]=[CH:12][CH3:13])[C@H:6]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([CH3:28])([CH3:27])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:16][C:15]=3[O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:5]2)[O:3]C1.Cl>O1CCOCC1>[CH2:30]([O:29][C:15]1[CH:16]=[C:17]([C:20]([CH3:27])([CH3:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:18]=[CH:19][C:14]=1[C@H:6]1[C@H:7]([CH2:10][CH:11]=[CH:12][CH3:13])[CH2:8][CH2:9][C:4](=[O:3])[CH2:5]1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86738160HCID 86738160, compound

Product 1

HCID 70529065HCID 70529065, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of trans-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-(2-butenyl)cyclohexanone ethylene ketal (700 mg, 1.38 mmole), dioxane (20 ml) and 2 N hydrochloric acid (20 ml) was heated at reflux for 1.5 hours. The reaction mixture was cooled, poured into ice water (500 ml) and extracted with ether (300 ml). The ether extract was washed with two 200 ml portions of saturated sodium bicarbonate, dried over magnesium sulfate and evaporated to give a quantitative yield of the title compound as an oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 hours
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with ether (300 ml)
  5. extractionThe ether extract
  6. washwas washed with two 200 ml portions of saturated sodium bicarbonate
  7. dry with materialdried over magnesium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-24afdff1a26843f7ac4735345b5a4c94
Source dataset
uspto-grants-1983_07
Patent number
US04391827

Reaction notes

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